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Fluorescence Behavior Associated with a Possible Intercolumnar Charge-transfer Interaction in the Crystalline State of a Dyad Consisting of Mesitylene and 1,4-Dicyano-2-methylnaphthalene Subunits

  • Ohta, Eisuke (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University) ;
  • Kobayashi, Hitoshi (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University) ;
  • Sakai, Atsushi (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University) ;
  • Matsui, Yasunori (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University) ;
  • Sato, Hiroyasu (Rigaku, Akishima) ;
  • Ikeda, Hiroshi (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University)
  • Received : 2015.05.22
  • Accepted : 2015.06.27
  • Published : 2015.06.30

Abstract

Fluorescence (FL) properties of a novel donor-acceptor dyad, comprised of mesitylene and 1,4-dicyano-2-methylnaphthalene (DCMN) subunits connected by an ether linkage, were elucidated. The dyad in cyclohexane exhibits FL arising from an intramolecular exciplex. In the crystalline state, the dyad does not emit light from intra- and inter-molecular exciplexes but rather displays FL that is nearly equivalent to that of 2-methoxymethyl-substituted DCMN. However, the emission spectrum of the crystalline dyad contains a shoulder in the long wavelength region, suggesting that weak intercolumnar charge-transfer interactions take place between columns consisting of the mesitylene and DCMN subunits.

Keywords

References

  1. Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Principles of Molecular Photochemistry An Introduction 2009, University Science Books: Herndon, VA.
  2. Mataga, N.; Okada, T.; Yamamoto, N. Chem. Phys. Lett. 1967, 1, 119-121 https://doi.org/10.1016/0009-2614(67)85003-6
  3. Beens, H.; Knibbe, H.; Weller, A. J. Chem. Phys. 1967, 47, 1183-1184. https://doi.org/10.1063/1.1712006
  4. Wang, Y.; Crawford, M. K.; Eisenthal, K. B. J. Phys. Chem. 1980, 84, 2696-2698 https://doi.org/10.1021/j100458a007
  5. Helsen, N.; Viaene, L.; Auweraer, M. V.; De Schryver, F. C. J. Phys. Chem. 1994, 98, 1532-1543 https://doi.org/10.1021/j100057a003
  6. Kawai, T.; Ikegami, M.; Arai, T. Chem. Commun. 2004, 824-825
  7. Cho, D. W.; Fujitsuka, M.; Choi, K. H.; Park, M. J.; Yoon, U. C.; Majima, T. J. Phys. Chem. B 2006, 110, 4576-4582. https://doi.org/10.1021/jp056078p
  8. Okada, T.; Fujita, T.; Kubota, M.; Masaki, S.; Mataga, N. Ide, R.; Sakata, Y.; Misumi, S. Chem. Phys. Lett. 1972, 14, 563-568 https://doi.org/10.1016/0009-2614(72)87208-7
  9. Masaki, S.; Okada, T.; Mataga, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1976, 49, 1277-1283 https://doi.org/10.1246/bcsj.49.1277
  10. Crawford, M. K.; Wang, Y.; Eisenthal, K. B. Chem. Phys. Lett. 1981, 79, 529-533 https://doi.org/10.1016/0009-2614(81)85030-0
  11. Verhoeven, J. W.; Scherer, T.; Willemse, R. J. Pure Appl. Chem. 1993, 65, 1717-1722
  12. Benten, H.; Ohkita, H.; Ito, S.; Yamamoto, M.; Tohda, Y.; Tani, K. Bull. Chem. Soc. Jpn. 2004, 77, 393-399. https://doi.org/10.1246/bcsj.77.393
  13. Mukae, H.; Maeda, H.; Mizuno, K. Angew. Chem., Int. Ed. 2006, 45, 6558-6560 https://doi.org/10.1002/anie.200602553
  14. Miyashi, T.; Kamata, M.; Mukai, T. J. Am. Chem. Soc. 1987, 109, 2780-2788 https://doi.org/10.1021/ja00243a035
  15. Miyashi, T.; Wakamatsu, K.; Akiya, T.; Kikuchi, K.; Mukai, T. J. Am. Chem. Soc. 1987, 109, 5270-5271. https://doi.org/10.1021/ja00251a037
  16. Imoto, M.; Ikeda, H.; Ohashi, M.; Takeda, M.; Tamaki, A.; Taniguchi, H.; Mizuno, K. Tetrahedron Lett. 2010, 51, 5877-5880. https://doi.org/10.1016/j.tetlet.2010.08.086
  17. Imoto, M.; Ikeda, H.; Fujii, T.; Taniguchi, H.; Tamaki, A.; Takeda, M.; Mizuno, K. Org. Lett. 2010, 12, 1940-1943. https://doi.org/10.1021/ol100324b
  18. Frisch, M. J. et al 2009, Gaussian 09 (Revision A.02), Gaussian Inc.: Pittsburgh, PA.
  19. Crystal information file can be obtained free of charge from The Cambridge Crystallographic Data Centre (CCDC-1052873) via www.ccdc.cam.ac.uk/data_request/cif.
  20. Ferraris, J.; Cowan, D. O.; Walatka, V. Jr.; Perlstein, J. H. J. Am. Chem. Soc. 1973, 95, 948-949 https://doi.org/10.1021/ja00784a066
  21. Keller, H. J. ed. Chemistry and Physics of One-Dimensional Metals 1977, Plenum, NY.
  22. Ikeda, H. et al unpublished data.

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